When we visted last December, our flight landed at almost 11pm (I actually was at work til about 6pm that day), I had booked a room at the Baymont Inn Orlando for one night thru Hotel Kingdom for less than $40. By the time we secured the rental and got to the hotel it was 12:30am anyways.It worked out fine as we had it planned that way, so we had packed in such a way that we would only need a couple of bags to go into the Baymont with us. Then the following morning we checked in early at the CR, it worked out perfect!
I would do it again if we were flying into MCO late night in the future.
Our trip earlier this month we drove, and did not make any reservations for the first night as we were not sure how far we would comfortably drive. As it turns out we drove the entire way to Orlando, leaving Chicago at 3:45am in the morning and arriving in Orlando at about midnight. I first called the POR where we where supposed to check in the following night and was told they could not accomodate us as the resort was at capacity (2000 rooms?). Later in the night, I attempted to call POR again and with said that my kids had their fingers crossed and my wife was sprinkling some pixie dust, is there anyway they could allow us to check in one night early. I paid the rack rate of $149.00 for the first night, my other nights were at $104.00 nightly, so this time I was willing to pay extra to not to have to move.... One of the factors that played into that was that we already had a split stay planned with the latter half at the Boardwalk... changing resorts 3 times in Orlando would not have been a lot of fun!
So, believe it or not we are considering re-visiting WDW in October, more than likely driving again, and if we do so, We will probably stay offsite for the first night or two, and then check in to our DVC resort for the rest of the stay.
Funny thing is, if you had asked us a year ago, I would have said we have never been to WDW! Gotta get maximum use out of those annual passes - three trips in one year!